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As far as I know you cannot use yum to upgrade between major versions of the OS. So you need to find some way start the system from external media to use anaconda or replace the complete content of your startup disk during the system restart.
Perhaps you could prepare the machine off-line. Then modify the initrd image on the old system to use the nc and dd utilities to replace the complete system disk over the network. I have never done it and no idea how feasible this was, but perhaps worth a thought.
Check the comments on above link: e.g. dd if=/dev/blah | ssh user@server dd of=/dev/target
When push comes to shove, and problems escalate.. and suddenly LOM access is wired and provided by remote on-site support staff, allowing remote console access and control, and the ablity to boot directly of OL5 media.
Oh well, as they say - do not look a gift horse in the mouth, or kick it in the nuts...